4-chloro-4-phenylbutanenitrile | 72335-16-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-chloro-4-phenylbutanenitrile
• CAS: 72335-16-1
• 化学式: C₁₀H₁₀ClN
• 分子量: 179.649
• InChiKey: TUGLOEJSSPWJMZ-UHFFFAOYSA-N

物化性质

• 熔点：
  126-128 °C
• 沸点：
  311.6±30.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-chloro-4-phenylbutanenitrile 、 4-(苄氧基)-2-羟基苯甲酸甲酯 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Discovery of phenoxybutanoic acid derivatives as potent endothelin antagonists with antihypertensive activity

  摘要：

  A series of phenoxybutanoic acid derivatives were synthesized and tested for their antagonistic activity on the contraction of the rat thoracic aortic ring induced by endothelin-1. Preliminary screening results showed that 6e and 6g with benzoheterocycles demonstrated significant antagonistic activities when compared to the reference compound BQ123. The results from additional assays for the binding affinity and selectivity for endothelin receptors showed that 6e was a selective ETA antagonist with a nanomolar IC50. Moreover, 6e was effective in relieving hypoxia-induced pulmonary arterial hypertension and right ventricular weight ratio. Therefore, 6e may have potential for further development as a therapeutic agent for the treatment of cardiovascular diseases. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.01.003
• 作为产物：
  描述：

  (+/-)-4-hydroxy-4-phenylbutanenitrile 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以69%的产率得到4-chloro-4-phenylbutanenitrile
  参考文献：
  名称：

  Discovery of phenoxybutanoic acid derivatives as potent endothelin antagonists with antihypertensive activity

  摘要：

  A series of phenoxybutanoic acid derivatives were synthesized and tested for their antagonistic activity on the contraction of the rat thoracic aortic ring induced by endothelin-1. Preliminary screening results showed that 6e and 6g with benzoheterocycles demonstrated significant antagonistic activities when compared to the reference compound BQ123. The results from additional assays for the binding affinity and selectivity for endothelin receptors showed that 6e was a selective ETA antagonist with a nanomolar IC50. Moreover, 6e was effective in relieving hypoxia-induced pulmonary arterial hypertension and right ventricular weight ratio. Therefore, 6e may have potential for further development as a therapeutic agent for the treatment of cardiovascular diseases. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.01.003

文献信息

• Silver-Catalyzed C(sp³)–H Chlorination
  作者：Jun Ozawa、Motomu Kanai

  DOI：10.1021/acs.orglett.7b00367

  日期：2017.3.17

  A silver-catalyzed chlorination of benzylic, tertiary, and secondary C(sp3)–H bonds was developed. The reaction proceeded with as low as 0.2 mol % catalyst loading at room temperature under air atmosphere with synthetically useful functional group compatibility. The regioselectivity and reactivity tendencies suggest that the chlorination proceeded through a radical pathway, but an intermediate alkylsilver

  开发了银催化的苄基，叔和仲C（sp 3）-H键的氯化反应。反应在室温下在空气气氛下以低至0.2mol％的催化剂负载量进行，具有合成上有用的官能团相容性。区域选择性和反应性趋势表明氯化是通过自由基途径进行的，但是不能排除中间的烷基银物种。
• Photocatalytic Atom‐Transfer Radical Addition of Activated Chlorides to Alkenes
  作者：Vladislav S. Kostromitin、Artem A. Zemtsov、Vitalij V. Levin、Alexander D. Dilman

  DOI：10.1002/adsc.202101047

  日期：2021.12.7

  A protocol for performing atom transfer radical addition of activated alkyl chlorides to alkenes is described. The reaction is promoted by blue light in the presence of an organic photocatalyst (3DPA2FBN), serving to generate free radicals, and a copper complex (IMesCuCl), which facilitates the chlorine transfer step. The reaction works efficiently with fluorinated and non-fluorinated α-chloroesters

  描述了一种用于将活化的烷基氯化物原子转移自由基加成到烯烃的协议。在有机光催化剂 (3DPA2FBN) 和铜络合物 (IMesCuCl) 存在下，有机光催化剂 (3DPA2FBN) 和促进氯转移步骤的铜络合物 (IMesCuCl) 存在下，通过蓝光促进反应。该反应适用于氟化和非氟化 α-氯酯。
• Copper-catalyzed radical ring-opening halogenation with HX
  作者：Shuai Liu、Ming Bai、Peng-Fei Xu、Qing-Xin Sun、Xin-Hua Duan、Li-Na Guo

  DOI：10.1039/d1cc03013b

  日期：——

  An efficient copper-catalyzed radical ring-opening halogenation with HX (aq) is described. This protocol features redox-neutral conditions, green halogen sources, and a broad substrate scope, providing practical access to distally chlorinated, brominated and iodinated alkyl ketones and alkyl nitriles with moderate to good yields.

  描述了一种有效的铜催化自由基开环卤化与 HX (aq)。该协议具有氧化还原中性条件、绿色卤素源和广泛的底物范围，为获得中等至良好收率的远端氯化、溴化和碘化烷基酮和烷基腈提供了实用的途径。
• Additions D'α-chloronitriles sur les olefines par catalyse redox
  作者：Marc Julia、Georgette Le Thuillier、Lucien Saussine

  DOI：10.1016/s0022-328x(00)92346-5

  日期：1979.9

  α-Chloronitriles are shown to add to α-olefins and conjugated dienes, with ferrous chloride or preferably cuprous chloride in the presence of 2,2′-bipyridyl or 1,10-phenanthroline as catalysts

  已显示在2,2'-联吡啶或1,10-菲咯啉的存在下，α-氯腈会与氯化亚铁或优选的氯化亚铜一起添加到α-烯烃和共轭二烯中
• Organocopper(<scp>ii</scp>) complexes: new catalysts for carbon–carbon bond formation <i>via</i> electrochemical atom transfer radical addition (<i>e</i>ATRA)
  作者：Miguel A. Gonzálvez、Chuyi Su、Craig M. Williams、Paul V. Bernhardt

  DOI：10.1039/d2sc03418b

  日期：——

  the organocopper(II) complex is to act as a source of masked radicals (in this case ˙CH2CN) that react with an alkene to generate the corresponding γ-halonitrile in good yields through atom transfer radical addition (ATRA) to various alkenes. The organocopper(II) complexes can be continuously regenerated electrochemically for ATRA (eATRA), which proceeds at room temperature, under low Cu loadings (1–10

  有机铜( II ) 配合物很少见，而有机铜( I ) 配合物在化学合成中很常见。在构建利用电化学生成有机铜 ( II ) 物种的策略的过程中，发现了一种形成具有 Cu II -C 键的化合物的方法，该方法在催化控制下对不同的官能化烯烃表现出非常有效的反应性。有机铜 ( II ) 络合物的作用是充当掩蔽自由基的来源（在这种情况下为 ˙CH 2 CN），通过原子转移自由基加成 (ATRA) 与烯烃反应生成相应的 γ-卤代腈，产率很高对各种烯烃。有机铜（Ⅱ) 配合物可以连续电化学再生 ATRA ( e ATRA)，其在室温下进行，在低铜负载量 (1-10 mol%) 下进行，并且有可能回收铜催化剂。